Hydrochloric Acid → 3,3'-Difluoro-4'-methoxymethoxy-4-propoxybiphenyl

HRID 1530758Notes

Reaction equation

HRID 1530758 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][O:10][CH3:11].OB(O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[C:17]([F:25])[CH:16]=1.Cl>[Pd].CO>[F:25][C:17]1[CH:16]=[C:15]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][O:10][CH3:11])=[C:2]([F:1])[CH:3]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 16217197(3-Fluoro-4-propoxyphenyl)boronic acidHCID 220320154-Bromo-2-fluoro-1-methoxymethoxy-benzene

Product 1

HCID 212524073,3'-Difluoro-4'-methoxymethoxy-4-propoxybiphenyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

First, 10.0 g (32.4 mmol) of 3,3′-difluoro-4′-methoxymethoxy-4-propoxybiphenyl [which was obtained by cross-coupling reaction of 3-fluoro-4-methoxymethoxybromobenzene with dihydroxy(3-fluoro-4-propoxyphenyl)borane in the presence of Pd catalyst], 50 ml of methanol, and 10 ml of a concentrated hydrochloric acid were heated to reflux for 3 hours. Then, 50 ml of water was added to the reaction solution and extracted with 150 ml of diethyl ether. The organic layer thus obtained was washed with a diluted aqueous sodium bicarbonate solution twice and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure to obtain 8.5 of a crude 3,3′-difluoro-4′- hydroxy-4-propoxybiphenyl. (Yield: 99.8%)

Sources & evidence

ORD record
ord-0cd52d0fa8164e559aa51f1e5ba697c9
Source dataset
uspto-grants-2001_03
Patent number
US06197217B1

Reaction notes

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